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Paper | Regular issue | Vol 55, No. 12, 2001, pp.2349-2359
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9349
Direct Modification of Benzoannelated Crown Ethers with 1,2,4-Triazin-5(2H)-one Moieties

Gennady L. Rusinov, Dmitry G. Beresnev, Nadezhda A. Itsikson, and Oleg N. Chupakhin*

*Institute of Organic Synthesis, Urals Division, Russian Academy of Sciences, 20, S. Kovalevskaya st., Yekaterinburg, GSP-147, 620219 , Russia

Abstract

A convenient method for one-step coupling of benzoannelated crown ethers with 1,2,4-triazinones based on the reaction of nucleophilic addition to unsubstituted carbon atom of the triazine ring has been worked out. It has been shown that the reaction of 3-substituted 1,2,4-triazin-5(2H)-ones (1) with benzocrown ethers (benzo-12-crown-4, benzo-15-crown-5, benzo-18-crown-6) in the presence of acetic or trifluoroacetic anhydride is accompanied by acylation of triazine ring and results in formation of 3-(1-acyl-5-oxo-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)benzocrown ethers (7-12). The latters were converted to 3-(5-oxo-2,5-dihydro-1,2,4-triazin-6-yl)benzocrown ethers (18-20) using two alternative routes: the elimination of acetic or trifluoroacetaldehyde or the deacylation followed by the oxidation of the 1,4,5,6-tetrahydro derivatives (13-15).